Ethyl 2-(1-hydroxy-1-cyclopentyl)-3-butenoate | 89922-32-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Ethyl 2-(1-hydroxy-1-cyclopentyl)-3-butenoate
• 英文别名: Ethyl 2-(1-hydroxycyclopentyl)-3-butenoate；ethyl 2-(1-hydroxycyclopentyl)but-3-enoate
• CAS: 89922-32-7
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: MVDNHMDFXIKWAG-UHFFFAOYSA-N

物化性质

• 沸点：
  268.4±15.0 °C(Predicted)
• 密度：
  1.075±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 2-(1-hydroxy-1-cyclopentyl)-3-butenoate 在 碘 、 silver trifluoromethanesulfonate 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以24%的产率得到2-Oxa-3-(iodomethyl)-4-carbethoxyspiro<3.4>octane
  参考文献：
  名称：

  Tandem Aldol-Cyclization Sequence for the Construction of Cyclic Ethers. The Formation of Substituted Tetrahydrofurans

  摘要：

  The application of a tandem deconjugative aldol-cyclization Sequence for the construction of substituted tetrahydrofurans was examined. The aldol condensation of alkenoates proceeded with alkylation at the alpha-position to generate homoallylic alcohol moieties. These compounds could be induced to cyclize under the influence of iodine via an endo mode. The stereoselectivity for the cyclization occurred in good to excellent fashion. X-ray crystal structure analysis of three of the tetrahydrofurans established unambiguously the product stereochemistry. This was: used to propose a transition structure for the cyclization which correctly predicts the observed product stereochemistry. By this method, virtually all the possible stereoisomers for the substituted tetrahydrofurans can be constructed by judicious choice of aldol product and/or olefin geometry.

  DOI：

  10.1021/jo00101a024
• 作为产物：
  描述：

  环戊酮 、 反式-2-丁烯酸乙酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 正己烷 为溶剂， 以56%的产率得到Ethyl 2-(1-hydroxy-1-cyclopentyl)-3-butenoate
  参考文献：
  名称：

  Tandem Aldol-Cyclization Sequence for the Construction of Cyclic Ethers. The Formation of Substituted Tetrahydrofurans

  摘要：

  The application of a tandem deconjugative aldol-cyclization Sequence for the construction of substituted tetrahydrofurans was examined. The aldol condensation of alkenoates proceeded with alkylation at the alpha-position to generate homoallylic alcohol moieties. These compounds could be induced to cyclize under the influence of iodine via an endo mode. The stereoselectivity for the cyclization occurred in good to excellent fashion. X-ray crystal structure analysis of three of the tetrahydrofurans established unambiguously the product stereochemistry. This was: used to propose a transition structure for the cyclization which correctly predicts the observed product stereochemistry. By this method, virtually all the possible stereoisomers for the substituted tetrahydrofurans can be constructed by judicious choice of aldol product and/or olefin geometry.

  DOI：

  10.1021/jo00101a024

文献信息

• Regioselectivity in the Reformatskii reaction of 4-bromocrotonate. Role of the catalyst and the solvent in the normal vs. abnormal modes of addition to carbonyl substrates
  作者：Leonard E. Rice、M. Craig Boston、Harry O. Finklea、Billy Jo Suder、James O. Frazier、Tomas Hudlicky

  DOI：10.1021/jo00184a042

  日期：1984.5
• RICE, L. E.;BOSTON, M. C.;FINKLEA, H. O.;SUDER, B. J.;FRAZIER, F. O.;HUDL+, J. ORG. CHEM., 1984, 49, N 10, 1845-1848
  作者：RICE, L. E.、BOSTON, M. C.、FINKLEA, H. O.、SUDER, B. J.、FRAZIER, F. O.、HUDL+

  DOI：——

  日期：——
• Tandem Aldol-Cyclization Sequence for the Construction of Cyclic Ethers. The Formation of Substituted Tetrahydrofurans
  作者：Paul Galatsis、Scott D. Millan、Patrik Nechala、George Ferguson

  DOI：10.1021/jo00101a024

  日期：1994.11

  The application of a tandem deconjugative aldol-cyclization Sequence for the construction of substituted tetrahydrofurans was examined. The aldol condensation of alkenoates proceeded with alkylation at the alpha-position to generate homoallylic alcohol moieties. These compounds could be induced to cyclize under the influence of iodine via an endo mode. The stereoselectivity for the cyclization occurred in good to excellent fashion. X-ray crystal structure analysis of three of the tetrahydrofurans established unambiguously the product stereochemistry. This was: used to propose a transition structure for the cyclization which correctly predicts the observed product stereochemistry. By this method, virtually all the possible stereoisomers for the substituted tetrahydrofurans can be constructed by judicious choice of aldol product and/or olefin geometry.